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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:31:20 UTC |
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Update Date | 2020-06-04 20:20:16 UTC |
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BMDB ID | BMDB0000479 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Methylhistidine |
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Description | N(pros)-Methyl-L-histidine, also known as 3-methylhistidine, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N(pros)-Methyl-L-histidine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N(pros)-Methyl-L-histidine exists in all eukaryotes, ranging from yeast to humans. |
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Structure | |
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Synonyms | Value | Source |
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(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid | ChEBI | 3-Methyl-L-histidine | ChEBI | N-pros-Methyl-L-histidine | ChEBI | (2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoate | Generator | 3-N-Methyl-L-histidine | HMDB | L-3-Methylhistidine | HMDB | N(pros)-Methyl-L-histidine | HMDB | N3-Methyl-L-histidine | HMDB | 3-Methylhistidine hydride | HMDB | 3-Methylhistidine dihydrochloride | HMDB | 3-Methylhistidine | ChEBI | Pi methylhistidine | HMDB | N(Pi)-methylhistidine | HMDB | N Pi-methylhistidine | HMDB |
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Chemical Formula | C7H11N3O2 |
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Average Molecular Weight | 169.1811 |
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Monoisotopic Molecular Weight | 169.085126611 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 368-16-1 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1 |
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InChI Key | JDHILDINMRGULE-LURJTMIESA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Histidine and derivatives |
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Alternative Parents | |
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Substituents | - Histidine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Imidazolyl carboxylic acid derivative
- Aralkylamine
- N-substituted imidazole
- Azole
- Imidazole
- Heteroaromatic compound
- Amino acid
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 200 mg/mL at 25 °C | BEILSTEIN | LogP | Not Available | Not Available |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Liver
- Longissimus Thoracis Muscle
- Milk
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 14 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 25 +/- 5 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 35 +/- 8 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 103 - 151 uM | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 2 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 35 +/- 9 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 19 +/- 4 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000479 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB093613 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 58494 |
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KEGG Compound ID | C01152 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 3-Methylhistidine |
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METLIN ID | 5466 |
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PubChem Compound | 64969 |
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PDB ID | Not Available |
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ChEBI ID | 27596 |
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References |
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Synthesis Reference | Ohba, Masashi; Mukaihira, Takafumi; Fujii, Tozo. Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines. Chemical & Pharmaceutical Bulletin (1994), 42(9), 1784-90. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
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